P-hydroxy phenone derivatives and the use thereof

Abstract

p-Hydroxy phenone derivatives of the general formula I ##STR1## where R 1 , R 2 and R 3 are identical or different and are methyl, chlorine, bromine and hydrogen, but R 1 , R 2 and R 3 are not all H, R 4 and R 5 are identical or different and are H, C 1 -C 4 -alkyl, or OR 6 , but R 4 and R 5 are not both H, X is a --CH═CH--, --CH 2 CH 2 or --CH 2 -- bridge, Y is a straight-chain or branched, saturated or unsaturated C 1 -C 4 bridge, and Z is NR 6 R 7 , where R 6 and R 7 are, independently of one another, hydrogen or C 1-4 -alkyl, or Z is a 5- or 6-membered ring with a nitrogen atom in the 1 position and, where appropriate, additionally a second N atom or an O or S atom, the second N atom being substituted by R 7 , as well as the physiologically tolerated salts thereof, are used to prepare drugs antiarrhythmic of Vaughan-Williams class III.

We claim: 
     
       1. A p-hydroxy phenone derivative of the formula I: ##STR6## where R 1 , R 2  and R 3  are identical or different and are methyl, chlorine, bromine or hydrogen, but R 1 , R 2  and R 3  are not all H; R 4  and R 5  are identical or different and are H, C 1  -C 4  alkyl, or OR 6 , but R 4  and R 5  are not both H; X is a --CH═CH--, --CH 2  CH 2  -- or --CH 2  -bridge; Y is a straight-chain or branched, saturated or unsaturated C 1  -C 4  bridge, and Z is NR 6  R 7 , where R 6  and R 7  are, independently of one another, C 104  -alkyl, or Z is pyrrolidinyl, piperidinyl or morpholinyl, as well as the physiologically tolerated salts thereof. 
     
     
       2. A p-hydroxy phenone derivative as claimed in claim 1, wherein R 1  and R 2  and CH 3  groups in the 3,5 positions and R 3  is H. 
     
     
       3. A p-hydroxy phenone derivative of the formula I ##STR7## where R 1 , R 2  and R 3  are identical or different and are methyl, chlorine, bromine and hydrogen, but R 1 , R 2  and R 3  are not all H, R 4  and R 5  are identical or different and are H, C 1  -C 4  -alkyl, or OR 6 , but R 4  and R 5  are not both H, X is a --CH═CH--, --CH 2  CH 2  or --CH 2  -- bridge, Y is a straight-chain or branched, saturated or unsaturated C 1  -C 4  bridge, and Z is pyrrolidinyl, as well as the physiologically tolerated salts thereof. 
     
     
       4. A pharmaceutical formulation useful as an anti-arrhythmic of Vaughan-Williams class III, comprising, as the active ingredient, a pharmaceutically effective amount of the p-hydroxyphenone derivative of claim 1 in combination with pharmaceutically acceptable excipients. 
     
     
       5. The formulation of claim 4, wherein the amount of said p-hydroxy phenone derivative ranges from 0.001 to 1% by weight. 
     
     
       6. The pharmaceutical formulation of claim 4, wherein said composition, as a single dose, contains from 10 to 500 mg of said p-hydroxy phenone derivative. 
     
     
       7. The pharmaceutical formulation of claim 4, which is effective as an anti-arrhythmic of Vaughan-Williams Class III.